2-Buten-1-amine → HCID 68614271, compound

HRID 1841588Notes

Reaction equation

HRID 1841588 reaction equation
[C:1]([O:5][C:6](=[O:23])[N:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br)=[CH:11][CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C[CH:25]=[CH:26][CH2:27][NH2:28].[CH3:29]C(N(C)C)=O>>[C:1]([O:5][C:6](=[O:23])[N:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:28]([CH2:27][CH:26]=[CH2:25])[CH3:29])=[CH:11][CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 304472-Buten-1-amineHCID 31374DimethylacetamideHCID 68615140HCID 68615140, compound

Product 1

HCID 68614271HCID 68614271, compoundYield 87%

Procedure

A solution of 40 g (103.7 mmol) of [4-(6-Bromo-hexyloxy)-phenyl]-methyl-carbamic acid tert-butyl ester in 400 ml DMA was treated at RT with 19.9 ml (207.4 mmol) of N-methylallylamine and stirred at RT for 22 h. The solution was concentrated and dissolved in aqueous saturated NaHCO3 /Et2O (3×). The organic phase was dried over Na2SO4 and evaporated. Flash column chromatography on silica gel with CH2Cl2/MeOH (95:5) yielded 33.9 g (87%) of {4-[6-(Allyl-methyl-amino)-hexyloxy]-phenyl}-methyl-carbamic acid tert-butyl ester, MS: 377 (MH+).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved in aqueous saturated NaHCO3 /Et2O (3×)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-65a6b1c185df4e07991857d33f78ff69
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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